期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 17, 期 29, 页码 8139-8144出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201003247
关键词
arginine; benzamides; galectins; molecular recognition; structure-activity relationships
资金
- Swedish Strategic Research Foundation
- Royal Physiographic Society in Lund
- foundation Olle Engkvist Byggmastare
Two series of C3-benzamido and O2-anion-substituted galactopyranosides were synthesized and studied as binders to arginine-rich proteins galectin-1, -3, -7, -8N (N-terminal domain), and -9N (N-terminal domain). The first series had a 4-methylbenzamide at C3 and the anionic O2-substituent was varied. The second series varied the 4-substituent of the C3-benzamide, whereas the anionic O2 substituent was kept as a sulfate. The influence of the O2-anion substituent correlated negatively with the oxygen charge density in case of galectin-1, -3, and -9N. In the second series, the electron-donating capacity of the 4-substituent of the C3-benzamides correlated positively with the magnitude of the affinity enhancement by the 2O-sulfate.
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